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Preparation method of toluenesulfonylurea

A technology of tosyl urea and p-toluene sulfonamide is used in the synthesis of important intermediates of sulfonylurea oral hypoglycemic drugs tolbutamide and gliclazide, and the preparation field of pharmaceutical intermediate p-toluene sulfonylurea, which can Solve the problems of slow progress and few reports, and achieve the effect of short reaction period, lower production cost and high product yield

Active Publication Date: 2013-03-13
广东逸舒制药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the research on the synthesis process route of p-toluenesulfonylurea at home and abroad is relatively active, but the progress is slow, and there are not many reports so far.

Method used

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  • Preparation method of toluenesulfonylurea

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Install a 1000ml three-necked bottle and a stirring oil bath heating device. Add 40 g of urea, 20 g of NaOH and 70 g of p-toluenesulfonamide in sequence, and heat up in an oil bath. Heating to above 130°C, the material is partially melted, start stirring, keep warm at 130-135°C, and react for about 100 minutes, the material liquid becomes thick enough to be unable to stir, stop stirring. Vacuum for 1 to 2 minutes to extract the ammonia gas generated by the reaction, and remove the oil bath. Add 700ml of drinking water, stir to dissolve, add 30% dilute sulfuric acid dropwise, adjust pH = 4, filter, rinse the filter cake with drinking water until pH = 5-6, discharge, crush, and dry at 100°C to obtain p-toluene Sulfonylurea 67.1g, purity 99.9%.

Embodiment 2

[0020] Install a 1000ml three-necked bottle and a stirring oil bath heating device. Add 40 g of urea, 20 g of NaOH and 70 g of p-toluenesulfonamide in sequence, and heat up in an oil bath. Heating to above 130°C, the material is partially melted, start stirring, keep warm at 135-140°C, and react for about 120 minutes, the material liquid becomes thick enough to be unable to stir, stop stirring. Vacuum for 1 to 2 minutes to extract the ammonia gas generated by the reaction, and remove the oil bath. Add 700ml of drinking water, stir to dissolve, add 30% dilute sulfuric acid dropwise, adjust pH = 4.5, filter, rinse the filter cake with drinking water until pH = 5-6, discharge, crush, and dry at 100°C to obtain p-toluene Sulfonylurea 66.9g, purity 99.0%.

Embodiment 3

[0022] Install a 1000ml three-necked bottle and a stirring oil bath heating device. Add 40 g of urea, 20 g of NaOH and 70 g of p-toluenesulfonamide in sequence, and heat up in an oil bath. Heat up to 130°C or above, the material is partially melted, start stirring, keep warm at 140-145°C, and react for about 95 minutes, the material liquid becomes thick enough to be unable to stir, stop stirring. Vacuum for 1 to 2 minutes to extract the ammonia gas generated by the reaction, and remove the oil bath. Add 700ml of drinking water, stir to dissolve, add 40% dilute sulfuric acid dropwise, adjust pH=4, filter, rinse the filter cake with drinking water until pH=5~6, discharge, crush, and dry at 100°C to obtain p-toluene Sulfonylurea 66.5g, purity 98.9%.

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PUM

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Abstract

The invention relates to the technical field of organic synthesis, and in particular relates to a preparation method of toluenesulfonylurea serving as a drug intermediate. The preparation method is characterized by comprising the following step: based on p-toluenesulfonamide (also know as 4-toluenesulfonamide) as a starting material, reacting with NaOH and urea to synthesize toluenesulfonylurea by a melting method which is also known as the dry method, wherein no reaction solvent is added. Toluenesulfonylurea is the important intermediate for synthesizing oral medication sulfonylurea such as tolbutamide and gliclazide.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, in particular to a method for preparing a drug intermediate p-toluenesulfonylurea, which is an important intermediate for synthesizing sulfonylurea oral hypoglycemic drugs tolbutamide and gliclazide . Background technique [0002] There are more than 150 million diabetic patients in the world, and it will gradually increase. There are about 50 million diabetic patients in my country, ranking second in the world. At present, oral hypoglycemic drugs commonly used in clinic mainly include α-glucosidase inhibitors, sulfonamides and biguanides, among which sulfonylurea hypoglycemic drugs are the most widely used class. [0003] Gliclazide and tolbutamide are mainstream hypoglycemic drugs at home and abroad, and they are used in large quantities. They are produced by major domestic pharmaceutical manufacturers. p-toluenesulfonylurea is used as an intermediate in the production of gli...

Claims

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Application Information

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IPC IPC(8): C07C311/58C07C303/40
Inventor 黄庆文黄庆雄邓军
Owner 广东逸舒制药股份有限公司
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